title: Insights into lomaiviticin biosynthesis. Isolation and structure elucidation of (-)-homoseongomycin.
abstract: The dimeric diazofluorenes known as the lomaiviticins are produced by the marine bacterium Salinispora pacifica DPJ-0019. Investigation of the fermentation broth of DPJ-0019 has yielded the first monomeric benzo[b]fluorene isolated from this species, (-)-homoseongomycin (13). (-)-Homoseongomycin (13) is related to the known natural product seongomycin (10), which is co-produced with the monomeric diazofluorenes known as the kinamycins. We describe the synthesis of the isotopically labeled derivative homoseongomycin-d5 (14), via the intermediacy of the diazofluorene "prelomaiviticin-d5" (12). Our studies establish that (-)-homoseongomycin (13) may be derived from prelomaiviticin (11) and suggest that 13 and 10 are shunt or detoxification metabolites in lomaiviticin and kinamycin biosynthesis, respectively.
authors.affiliation: Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
authors.forename: Christina M
authors.initials: CM
authors.lastname: Woo
authors.forename: Shivajirao L
authors.initials: SL
authors.lastname: Gholap
authors.forename: Seth B
authors.initials: SB
authors.lastname: Herzon
mesh_terms: D005449:Fluorenes / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D008386:Marine Biology; D008848:Micromonosporaceae / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D000095602:Angucyclines and Angucyclinones
chemical_list: D005449:Fluorenes; C584040:homoseongomycin; C433842:lomaiviticin A; D000095602:Angucyclines and Angucyclinones; C433843:lomaiviticin B